Cytotoxic sesquiterpenoids from Ligularia pleurocaulis

• Published in: Phytochemistry (Oxford) Vol. 125; pp. 99 - 105
• Main Authors: Xie, Guang-Bo, Xie, Ya, Hu, Yang-Zhirong, Zhu, Zhi-Xiang
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.05.2016; Elsevier
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Apoptosis - drug effects; Asteraceae - chemistry; Biligupleurolide; Biochemistry & Molecular Biology; Compositae; Cu Kα X-ray crystallography; Cytotoxicity; Drug Screening Assays, Antitumor; Female; Hep G2 Cells; Humans; Life Sciences & Biomedicine; Ligularia pleurocaulis; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Sciences; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; Sesquiterpenoid; Cytotoxicity; Ligularia pleurocaulis; Compositae; Cu Kα X-ray crystallography; Biligupleurolide; Sesquiterpenoid; OCCURRING TERPENE DERIVATIVES; KANGTINGENSIS; EREMOPHILANE-TYPE SESQUITERPENOIDS; Cu K alpha X-ray crystallography; RHIZOMES
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2016.02.010

Five sesquiterpenoids, including an eremophilenolide dimer (1), were isolated from whole plants of Ligularia pleurocaulis. Together with eight known sesquiterpenoids, all 13 compounds were evaluated for their cytotoxicity against three cancer cell lines (MCF-7, HepG2 and A549) by the MTT assay, where 1 showed moderate activities with IC50 in the range of 5.2–8.4μM. [Display omitted] •Thirteen sesquiterpenoids, including five previously unknown compounds, were isolated from Ligularia pleurocaulis.•Their structures were elucidated by the analysis of data from NMR spectroscopy and X-ray crystallography.•One previously unknown compound showed moderate cytotoxic activities against HepG2, A549 and MCF-7 cells. The phytochemical investigation of whole plants of Ligularia pleurocaulis led to isolation of five sesquiterpenoids, including an eremophilenolide dimer named biligupleurolide, along with eight known sesquiterpenoids. Their structures were determined by spectroscopic methods including 2D NMR techniques, and the structures of biligupleurolide and ligupleurolide were confirmed by X-ray diffraction analysis. All of the isolated compounds were tested for their cytotoxic activity against three cancer cell lines (HepG2, A549 and MCF-7), and biligupleurolide showed moderate inhibitory activities, with IC50 values of 5.2, 5.6 and 8.4μM against MCF-7, HepG2 and A549, respectively.